US3239503A - Azido benzenesulfonyl semicarbazides - Google Patents

Azido benzenesulfonyl semicarbazides Download PDF

Info

Publication number: US3239503A
Authority: US; United States
Prior art keywords: benzenesulfonyl; azido; semicarbazide; grams; hydrazine
Prior art date: 1961-08-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

US218106A

Other languages

English (en)

Inventor

Korger Gerhard

Weyer Rudi

Aumuller Walter

Haack Erich

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1961-08-22

Filing date

1962-08-20

Publication date

1966-03-08

1961-08-22 Priority claimed from DE1961F0034750 external-priority patent/DE1237120B/de

1961-10-05 Priority claimed from DEF35063A external-priority patent/DE1262281B/de

1962-08-20 Application filed by Hoechst AG filed Critical Hoechst AG

1966-03-08 Application granted granted Critical

1966-03-08 Publication of US3239503A publication Critical patent/US3239503A/en

1983-03-08 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

MTJYNJOJOXNCEC-UHFFFAOYSA-N N(=[N+]=[N-])N(NC(=O)N)S(=O)(=O)C1=CC=CC=C1 Chemical class N(=[N+]=[N-])N(NC(=O)N)S(=O)(=O)C1=CC=CC=C1 MTJYNJOJOXNCEC-UHFFFAOYSA-N 0.000 title 1
-1 alkyl radicals Chemical class 0.000 description 21
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
235000013877 carbamide Nutrition 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000012948 isocyanate Substances 0.000 description 7
238000000034 method Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
150000008331 benzenesulfonamides Chemical class 0.000 description 5
GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000000126 substance Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
150000007513 acids Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000002429 hydrazines Chemical class 0.000 description 3
230000002218 hypoglycaemic effect Effects 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000155 melt Substances 0.000 description 2
UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
QGJUAGKXYDNBAE-UHFFFAOYSA-N (4-azidophenyl)sulfonylurea Chemical compound N(=[N+]=[N-])C1=CC=C(C=C1)S(=O)(=O)NC(=O)N QGJUAGKXYDNBAE-UHFFFAOYSA-N 0.000 description 1
WIUQFCKUUQIUQD-UHFFFAOYSA-N (isocyanatohydrazinylidene)-oxomethane Chemical class O=C=NNN=C=O WIUQFCKUUQIUQD-UHFFFAOYSA-N 0.000 description 1
ASRMWYDEZPXXBA-UHFFFAOYSA-N (sulfonylamino)urea Chemical class NC(=O)NN=S(=O)=O ASRMWYDEZPXXBA-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IXSGUIFSMPTAGW-UHFFFAOYSA-N 2-(trifluoromethyl)benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1C(F)(F)F IXSGUIFSMPTAGW-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
TVHXQQJDMHKGGK-UHFFFAOYSA-N 4-(trifluoromethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 TVHXQQJDMHKGGK-UHFFFAOYSA-N 0.000 description 1
UZEFHQIOSJWWSB-UHFFFAOYSA-N 4-azidobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(N=[N+]=[N-])C=C1 UZEFHQIOSJWWSB-UHFFFAOYSA-N 0.000 description 1
UQUHQKVINDTPNE-UHFFFAOYSA-N 4-methylpiperidin-1-amine Chemical compound CC1CCN(N)CC1 UQUHQKVINDTPNE-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
UGBKOURNNQREPE-UHFFFAOYSA-N azepan-1-amine Chemical compound NN1CCCCCC1 UGBKOURNNQREPE-UHFFFAOYSA-N 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
239000002585 base Substances 0.000 description 1
JWPWVPPTDSULMI-UHFFFAOYSA-N benzenesulfonamidothiourea Chemical class NC(=S)NNS(=O)(=O)C1=CC=CC=C1 JWPWVPPTDSULMI-UHFFFAOYSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001714 carbamic acid halides Chemical class 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006477 desulfuration reaction Methods 0.000 description 1
230000023556 desulfurization Effects 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000005187 foaming Methods 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
WEPOCRSIOTVGAH-UHFFFAOYSA-N hydrazinyl hydrogen carbonate Chemical class NNOC(O)=O WEPOCRSIOTVGAH-UHFFFAOYSA-N 0.000 description 1
HTHDATSBFYFYTK-UHFFFAOYSA-N hydrazinyloxymethanethioic S-acid Chemical class N(N)OC(O)=S HTHDATSBFYFYTK-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
VDUYDMJCLBXKNB-UHFFFAOYSA-N methyl N-(4-azidophenyl)sulfonylcarbamate Chemical compound COC(NS(=O)(=O)C1=CC=C(C=C1)N=[N+]=[N-])=O VDUYDMJCLBXKNB-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000002832 nitroso derivatives Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
150000003349 semicarbazides Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members

Definitions

the desired compounds may be obtained from correspondingly substituted benzenesulfonyl carbamic acid halides and N,N-alkylene-hydrazines, or vice versa from N,N-alkylene-hydrazino-N'- carbonic acid halides and the corresponding benzenesulfonamides.
benzenesulfonyl ureas which are unsubstituted on the side of the urea molecule opposite to the sulfonyl group, or monoor disubstituted by other low molecular alkyl or aryl radicals may be converted into the desired compounds when reacted with N,N-alkylene-hydrazines per se or in the form of their salts.
starting materials there may be used as starting materials 0, m, p-azido or trifluoromethylbenzenesulfonic acid derivatives, such as isocyanates, amides, carbamic acid esters, ureas and thioureas.
the products are separated as completely as possible from the benzenesulfonamides used as starting substances or formed in the course of the reaction.
This separation may be favourably effected by taking up the products according to the invention in strongly diluted ammonia, filtering off any undissolvecl matter and recovering the desired products by acidification, advantageously by means of organic acids such as dilute acetic acid.
the 4-benzenesulf0nyl-l,1-alkylene semic-arbazides obtained according to the process of the present invention are valuable medicaments which are characterized, in particular, by a strong hypoglycemic action and very low toxicity.
a lowering of the blood sugar level by 30% could still be detected 24 hours after the peroral application of 4-(4-azido-benzenesulfonyl)-1,1-(- -methylpentamethylene)-semicarbazide or of 4-(4-azido-benzenesulfonyl)-l,1-hexamethylene-semicarbazide to a rabbit .sugar level by the application of an essentially smaller number of single doses.
medicinal preparations there enter into consideration preferably tablets containing the products of the invention and, in addition thereto, the usual adjuvants and carriers such as for example, talc, starch, lactose, tragacanth or magnesium stearate.
adjuvants and carriers such as for example, talc, starch, lactose, tragacanth or magnesium stearate.
Example 1 4-(4-azid0-benzenesulfonyl -J ,1 -hexamethylene-semicarbazide 32.4 grams of, N-(4-azido-benzenesulfonyl)-carbamic acid methyl ester were mixed with 13 grams of N,N-pentamethylene-hydrazine and heated for 30 minutes at 125 C. on the oil bath. The reaction product was then recrystallized twice from acetic ester. There was obtained the 4 (4 azido-benzenesulfonyl)-l,l-pentamethylene-semicarbazide melting at 17017l C. (with decomposition). With the meet N,N-tetramethylene-hydrazine there was obtained in an analogous manner the 4-(4-azidobenzenesulfonyl)-l,1-tetramethylene-semicarbazide.
hexamethylene-semicarbazide 28.3 grams of m-(trifluoromethyl-benzenesulfonyl)- carbamic acid methyl ester were mixed with 11.4 grams of N-amino-hexamethylene-imine and heated for 30 minutes at 120 C. on the oil bath. First a melt was formed which solidified subsequently. After cooling, the 4-(3-trifluoromethyl benzenesulfonyl)-1,l-hexamethylene-sermcarbazide was recrystallized, from water/ethanol and' melted at 159-16l C.
Example 7.'-.-4-(3-triflu0romethyl-benzenesulfonyl)-1,1- pentamethylene-semicarbazide 9.7 grams of m-(trifiuoromethyl-benzenesulfonyl)-isocyanate were dissolved .in 30cc. of absolute ether and slowly added dropwisewhile cooling and shaking-.to a solution of 5 grams of, N-amino-piperidine in about 30 cc. of absolute ether.
Example 8.4-(4-azido-bertzenesulfonyl)-1,1-hexamethylene-semicarbazide 24.1 grams of, N-(4-azido-benzenesulfonyl)-urea melting point 168-170 C. (prepared by reacting 4-aZidoI-ben-' 1 zenesulfonamide with potassium cyanate .in boiling aqueous ethanol) were boiled under reflux for 1 hour in 250 cc.

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

US218106A 1961-08-22 1962-08-20 Azido benzenesulfonyl semicarbazides Expired - Lifetime US3239503A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE1961F0034750 DE1237120B (de)	1961-08-22	1961-08-22	Verfahren zur Herstellung von 4-Benzolsulfonyl-1, 1-alkylensemicarbaziden
DEF0034822		1961-08-31
DEF35063A DE1262281B (de)	1961-10-05	1961-10-05	Verfahren zur Herstellung von 4-Benzolsulfonyl-1, 1-hexamethylensemicarbazid

Publications (1)

Publication Number	Publication Date
US3239503A true US3239503A (en)	1966-03-08

Family

ID=27210235

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US218106A Expired - Lifetime US3239503A (en)	1961-08-22	1962-08-20	Azido benzenesulfonyl semicarbazides

Country Status (6)

Country	Link
US (1)	US3239503A (de)
CH (3)	CH438305A (de)
DK (1)	DK102961C (de)
FR (3)	FR2203M (de)
GB (1)	GB1014424A (de)
NL (1)	NL282365A (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3689649A (en) *	1970-07-16	1972-09-05	Henri Dietrich	N-substituted n-arylsulfonyl ureas for producing a hypoglycaemic effect
US3939269A (en) *	1971-04-26	1976-02-17	Hoechst Aktiengesellschaft	Benzenesulfon YL-semicarbazides for lowering blood sugar levels

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3015673A (en) *	1956-09-28	1962-01-02	Swiss Serum And Vaccine Inst	New urea derivatives and preparation thereof
US3063903A (en) *	1961-03-29	1962-11-13	Upjohn Co	Novel n-arylsulfonyl n'-(cyclicamino) ureas and oral antidiabetic compositions containing said novel compounds

0
- NL NL282365D patent/NL282365A/xx unknown
1962
- 1962-08-20 US US218106A patent/US3239503A/en not_active Expired - Lifetime
- 1962-08-20 CH CH1781166A patent/CH438305A/de unknown
- 1962-08-20 CH CH993262A patent/CH427793A/de unknown
- 1962-08-20 CH CH1781266A patent/CH438304A/de unknown
- 1962-08-21 DK DK441363AA patent/DK102961C/da active
- 1962-08-22 GB GB32297/62A patent/GB1014424A/en not_active Expired
- 1962-11-21 FR FR916114A patent/FR2203M/fr active Active
- 1962-11-21 FR FR916113A patent/FR2202M/fr active Active
- 1962-11-21 FR FR916115A patent/FR2214M/fr active Active

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3015673A (en) *	1956-09-28	1962-01-02	Swiss Serum And Vaccine Inst	New urea derivatives and preparation thereof
US3063903A (en) *	1961-03-29	1962-11-13	Upjohn Co	Novel n-arylsulfonyl n'-(cyclicamino) ureas and oral antidiabetic compositions containing said novel compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3689649A (en) *	1970-07-16	1972-09-05	Henri Dietrich	N-substituted n-arylsulfonyl ureas for producing a hypoglycaemic effect
US3939269A (en) *	1971-04-26	1976-02-17	Hoechst Aktiengesellschaft	Benzenesulfon YL-semicarbazides for lowering blood sugar levels

Also Published As

Publication number	Publication date
CH427793A (de)	1967-01-15
FR2214M (fr)	1963-12-16
NL282365A (de)
GB1014424A (en)	1965-12-22
FR2203M (fr)	1963-12-09
DK102961C (da)	1965-11-01
FR2202M (fr)	1963-12-09
CH438304A (de)	1967-06-30
CH438305A (de)	1967-06-30

Publication	Publication Date	Title
US3668215A (en)	1972-06-06	Aryl-sulphonyl-semicarbazides containing heterocyclic acylamino groups
US3406199A (en)	1968-10-15	Benzenesulfonyl ureas and process for their manufacture
US3239503A (en)	1966-03-08	Azido benzenesulfonyl semicarbazides
US4132795A (en)	1979-01-02	Benzenesulfonyl ureas and their use for the treatment of diabetes mellitus
US3754030A (en)	1973-08-21	N - (4-(beta-<2-methoxy-5-chloro-benzamido>-ethyl) - benzenesulfonyl)-n'-cyclopentyl-urea and process for its manufacture
CA1211106A (en)	1986-09-09	Benzenesulfonyl-ureas and processes for preparing them
US3843661A (en)	1974-10-22	Benzene-sulfonyl semicarbazides
US3752818A (en)	1973-08-14	Sulphonyl ureas and sulphonyl semicarbazides containing heterocyclic acyl amino groups and their production
US3336322A (en)	1967-08-15	Benzenesulfonyl ureas and process for their manufacture
US3829434A (en)	1974-08-13	Piperidinesulfonylurea derivatives
KR880002706B1 (ko)	1988-12-26	설포닐 우레아의 제조방법
US3449346A (en)	1969-06-10	Benzenesulfonyl ureas
US3835188A (en)	1974-09-10	Benzenesulfonyl-ureas and process for their preparation
US3454636A (en)	1969-07-08	Benzenesulfonyl-ureas and process for their manufacture
US3448149A (en)	1969-06-03	Benzenesulfonyl ureas
US3813398A (en)	1974-05-28	Benzenesulfonyl-semicarbazides and process for their manufacture
US3097240A (en)	1963-07-09	Novel sulfonyl-ureas
US3510496A (en)	1970-05-05	Benzenesulfonyl-ureas with hypoglycemic activity
US3917690A (en)	1975-11-04	Benzenesulfonyl ureas and process for their manufacture
US3607935A (en)	1971-09-21	Sulfonyl-ureas and a process for preparing them
US3435116A (en)	1969-03-25	The treatment of diabetes mellitus with benzenesulfonyl ureas
US3932658A (en)	1976-01-13	Composition and method for lower blood sugar containing N-[4-(β-<2-methoxy-5-chloro-benzamido>-ethyl)-benzenesulfonyl]-N'-cyclopentyl-urea
US3202680A (en)	1965-08-24	New benzenesulfonyl ureas and process for their manufacture
US3420882A (en)	1969-01-07	Benzenesulfonyl ureas
US3709908A (en)	1973-01-09	Benzenesulfonyl ureas having hypoglycemic activity

US3239503A - Azido benzenesulfonyl semicarbazides - Google Patents

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